Best made his debut for the Cayman Islands in the Red Stripe Bowl, a domestic competition in the West Indies, in October 2000. He played four matches in the tournament, making up his only four List A matches to date.[5] He played in the ICC Americas Championship in 2002 and 2004 and in the repêchage tournament for the 2005 ICC Trophy in 2005.[7] In the latter tournament, he won man of the match awards for his performances against Kuwait and Zambia,[8] finishing the tournament with the best batting average (76.33) and the second highest score of 99 not out.[9]
In August 2005 he played his, to date, only first-class matches, 2005 ICC Intercontinental Cup matches against Bermuda and Canada.[4] In 2006, he played for the Cayman Islands in the inaugural Stanford 20/20 tournament. He top scored with 74 in the preliminary round against the Bahamas, winning $25,000 for the man of the match award,[10] but only scored three in the first round proper against Trinidad & Tobago as the Caymans were knocked out of the tournament.[11] Only three players made a higher individual score in the tournament.[12]
Later in 2006, he again played in the Americas Championship.[7] He was the second highest scorer in the tournament,[13] winning the man of the match award for his top score of 116 against Argentina.[14] He most recently represented the Cayman Islands at Division Three of the World Cricket League in Darwin, Australia in May/June 2007.[15]